The present invention relates to a class of sulfonylurea compounds which are herbicidal sulfonamides, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants, as well as for agriculturally suitable salts.
U.S. Pat. No. 4,127,405 and U.S. Pat. No. 4,169,719 disclose herbicidal benzenesulfonylureas.
U.S. Pat. No. 4,394,506 and U.S. Pat. No. 4,383,113 disclose ortho-alkoxycarbonylbenzenesulfonylureas.
U.S. Pat. No. 4,370,479 discloses herbicidal naphthalene sulfonylureas.
U.S. Pat. No. 4,435,206 and EP-A-No. 35,893 disclose herbicidal pyridylsulfonylureas.
EP-A-No. 30,142 discloses thiophene sulfonylureas which are useful as herbicides.
U.S. Pat. No. 4,420,325 discloses herbicidal benzylsulfonylureas.
U.S. Ser. No. 533,341 discloses the herbicidal sulfonylureas of the following general structure: ##STR1##
South African Patent Application No. 83/5165 filed by Ciba-Geigy (Swiss priority 7/16/82) discloses herbicidal benzo[b]furan sulfonylureas.
South African Application No. 83/8416 (Swiss priority 11/12/82; published 5/12/84) discloses sulfonylureas of the general formula ##STR2## wherein Z is O or S;
E is N or CH; PA0 R.sub.1 is, inter alia, H, halogen, NO.sub.2, C.sub.1 -C.sub.4 alkyl, etc.; PA0 R.sub.3 and R.sub.4 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, --NR.sub.5 R.sub.6, etc.; PA0 R.sub.5 and R.sub.6 are H or C.sub.1 -C.sub.4 alkyl; and PA0 A is an unsaturated or partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms. PA0 Z is O or S; PA0 E is CH or N; PA0 R.sub.1 is, inter alia, H, halogen, NO.sub.2, CN, etc.; PA0 R.sub.2 is, inter alia, H, halogen, C.sub.1 -C.sub.4 alkyl, etc.; PA0 R.sub.3 and R.sub.4 are independently H, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 haloalkoxy, --NR.sub.12 R.sub.13, etc.; and PA0 R.sub.12 and R.sub.13 are independently H or C.sub.1 -C.sub.4 alkyl, PA0 R.sub.1 is, inter alia, H, halogen, NO.sub.2, CN, etc.; PA0 R.sub.2 is, inter alia, H, halogen, C.sub.1 -C.sub.4 alkyl, etc.; PA0 Z is O or S; PA0 R.sub.3 and R.sub.4 are independently H, halogen, C.sub.1 -C.sub.4 haloalkoxy, NR.sub.19 R.sub.20, etc.; PA0 R.sub.19 and R.sub.20 are independently H or C.sub.1 -C.sub.4 alkyl; PA0 R.sub.9 is, inter alia, H, halogen, C.sub.1 -C.sub.4 alkyl, etc.; PA0 R.sub.10 is H, halogen or CH.sub.3 ; and PA0 R.sub.11 is, inter alia, a radical C(O)R.sub.24 or a C.sub.1 -C.sub.4 alkyl group that is mono- or poly-substituted by CN, NO.sub.2, OH, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, etc. PA0 R.sub.5 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 CN or CH.sub.2 CH.sub.2 CN; and PA0 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, etc. PA0 L is ##STR7## R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.10, SO.sub.2 NR.sub.11 R.sub.12, SO.sub.2 N(OCH.sub.3)CH.sub.3, S(O).sub.n R.sub.13, CH.sub.2 OCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, C.sub.6 H.sub.5 or Q; PA0 Q is ##STR8## R.sub.2 is H, F, Cl, Br, CF.sub.3, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3 or SC.sub.2 H.sub.5 ; PA0 R.sub.3 is H, CH.sub.3, OCH.sub.3, F, Cl, Br, SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3 or S(O).sub.n CH.sub.3 ; PA0 R.sub.4 is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, F, Cl, Br, SO.sub.2 NR.sub.11 R.sub.12, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.13 ; PA0 R.sub.5 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.10, SO.sub.2 NR.sub.11 R.sub.12, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.13 ; PA0 R.sub.6 is CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3 or SO.sub.2 CH.sub.2 CH.sub.3 ; PA0 R.sub.7 is H, C.sub.1 -C.sub.5 alkyl, CH.sub.2 CH.sub.2 F, CH.sub.2 CH.sub.2 CH.sub.2 F, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.3 OCH.sub.2 CH.sub.2 or C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 ; PA0 R.sub.8 is H, Cl, CH.sub.3 or OCH.sub.3 ; PA0 R.sub.9 is H or CH.sub.3 ; PA0 R.sub.10 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; PA0 R.sub.11 is H or C.sub.1 -C.sub.2 alkyl; PA0 R.sub.12 is C.sub.1 -C.sub.2 alkyl; PA0 R.sub.13 is C.sub.1 -C.sub.3 alkyl; PA0 n is 0, 1 or 2; PA0 X is NR.sub.14 R.sub.15 ; PA0 R.sub.14 is H or C.sub.1 -C.sub.2 alkyl; PA0 R.sub.15 is C.sub.1 -C.sub.2 alkyl, OCH.sub.3, OC.sub.2 H.sub.5 or CH.sub.2 CN; PA0 Y is OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2 or OCH.sub.2 CF.sub.3 ; and PA0 Z is CH or N; PA0 (1) Compounds of Formula I wherein PA0 (2) Compounds of Preferred 1 wherein PA0 (3) Compounds of Preferred 2 wherein PA0 (4) Compounds of Preferred 3 wherein PA0 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]aminocarb onyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 195.degree.-197.degree. C.(d); and PA0 2-[[[4-(methylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]aminocarb onyl]aminosulfonyl]benzoic acid, ethyl ester, m.p. 181.degree.-183.degree. C.(d).
South African Application No. 84/2245 (Swiss priority 3/28/83; published 9/28/84) discloses herbicidal sulfonylureas of the formula ##STR3## wherein A is C.sub.1 -C.sub.6 haloalkyl;
South African Application No. 84/2722 (Swiss priority 4/13/83; published 10/13/84) discloses sulfonylureas of the formula ##STR4## wherein A is a radical of the formula --CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
South African Application No. 82/7439, published 4/13/83, discloses the following compounds of the formula ##STR5## wherein R.sub.4 is H, CH.sub.3 or C.sub.2 H.sub.5 ;
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.